


On the Line

by bideanie



Category: Supernatural
Genre: Fluff, M/M, Matchmaker Charlie, Oblivious Dean, Radio Host Dean, Valentine's Day, Writer Castiel
Language: English
Status: Completed
Published: 2015-02-14
Updated: 2015-02-14
Packaged: 2018-03-12 21:05:12
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,276
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3355235
Author URL: https://archiveofourown.org/users/bideanie/pseuds/bideanie
Summary: <blockquote class="userstuff">
              <p>❤ happy valentine's day/national fanworks day! ❤</p><p>Dean is a radio DJ/host, and for the past few months, he's been getting calls from a man named Cas. Dean quickly begins to like Cas, and is excited every time Charlie tells him that Cas has called once again. Charlie, and most of the listeners, think that Dean and Cas should get together and fall in love.</p><p>They've yet to meet, but Valentine's day, awkward advice and matchmaker!charlie may change that...</p>
            </blockquote>





	On the Line

Dean doesn’t have a crush on the guy, or anything, but he couldn’t help hoping that he would call in sometime. It _was_ Valentine’s day, after all.

Dean’s caller friend seemed like the romantic type that would have a lot to say about V-day; good or bad. Dean knew he didn’t have a boyfriend, so there was a slight chance he’d be listening to Dean’s morning show, and not off on some romantic date.

Charlie, Dean’s technician-slash-assistant-slash-nerd-slash-bestfriend, had tracked down the guy’s cell phone, and had informed Dean that he lived in San Francisco, like them. Dean had been mad at her for a whole six hours after he found out what she'd done, claiming it was stalker-y like the chick from Sleepless in Seattle, but Charlie won him back after buying him lunch.

Dean couldn't deny that he wished he knew more about the guy. Cas had been calling in to Dean’s show for six months, and even though Dean knew the quirky facts about him, like his undying love for bees and cats, or the fact he was a published poet, or that he had a brother that may or may not be a porn star, Dean did not know whether he had a freckle near his belly button, or if his nose scrunched up when he was annoyed, or if his gums showed when he smiled.

Dean would do anything to find out more about him, but he’d accepted the fate that they would forever be restricted to a DJ-listener relationship. That didn’t, however, stop Dean’s heart skipping a beat whenever Charlie told him that Cas was on the line.

“That was REO Speedwagon with _can’t fight this feeling,_ which my annoying bartender friend Jo Harvelle told me to play or she would stop serving me when I go to the Roadhouse, which is a great bar by the way, and seeing as it’s Valentine’s Day, it’s pretty much written in the stars that I’m gonna go out tonight.” Dean grinned. Jo had even promised to get him a pie if he played the song for her. Who needed a boyfriend on Valentine’s when you had single friends who got you pie?

Charlie hissed out a _Dean! No advertising!_ Dean carried on, ignoring her. It wasn’t as though the station’s manager was going to cuss him out for it, seeing as the station manager was a frequent member of the Roadhouse community.

“Now onto some _real_ music, no offense to REO, and Charlie’s been badgerin’ me to play some cutesy romance crap, so here’s _wish you were here_ by Pink Floyd.”  Dean pushed his headphones down so they wrapped around his neck.

“Any callers, Char?” Dean called to his friend, who was sat in the room next door, separated by a glass window.

Charlie got up and went to stand by the open doorway next to the window. “No, Dean, you’re dreamy lover boy hasn’t called.”

Dean had to bite his tongue to stop himself from sighing.

“Th-that’s not what I meant. I have other callers, y’know.” Dean stammered. Charlie fixed him with a plain stare, trying to make Dean cave, but to no avail.

“He’ll call, Dean. It’s Valentine’s! And you do have the morning show. He might have slept in.” Charlie shrugged, eyes flicking up to the clock which read 10:39.

“He’s never slept in bef- shut up, Charlie! I wasn’t talking about him.” Dean protested, blush rising on his cheeks. He was pretty transparent when it came to men. Around women, Dean was full of charm and ease, but when it came to men? He was basically the human equivalent of chunky peanut butter; not smooth _whatsoever._

“Dean, you ask me every day for calls, but once you’ve spoken to him, you’re little miss quiet and satisfied. Just admit you’re waiting for his call!” Charlie exclaimed, looking excited. She’d already announced months ago that she _shipped_ Dean and Cas, and apparently, a bunch of the listeners did, too. For Christmas, Charlie had painted Dean a very realistic picture of himself kissing a black silhouette with a question mark in place of a face. _When you finally grow some balls and meet the guy, I’ll re-paint it!_ Charlie had told him.

“What if he’s calling right now while you’re here talking to me?” Dean’s eyes widened in panic.

Charlie rolled her eyes. “Don’t get your panties in a twist, Winchester.”

Dean almost choked, wondering how Charlie had found out, but then realised she had just been joking. _Thank god_.

Charlie retreated back to her desk just ask the final notes of the song played, and Dean went back to full DJ mode.

“So, how are you guys liking Valentine’s so far?” Dean asked conversationally. Sometimes Cas would call in if Dean had asked the listeners a specific question or was talking about a certain topic, and hoped that it would happen today, too. “I gotta admit, I’m not really a fan. I used to be, when I was young and wild. I used to call it unattached drifter Christmas.” Dean paused. “Those were the good days, eh?”

Through the window, Dean saw Charlie roll her eyes.

“Charlie’s rolling her eyes at me. What? Like you’ve never been young and crazy, Charlene. Dare I remind you of that time we went to Comic Con?”

Charlie hid her face behind her hands.

“Anyway, I wanna hear about your Valentine’s Day! I’m gonna put on another song, and when I get back I’ll read out some texts and maybe answer a few calls. This is for all you singles tonight, the unattached drifter theme song, _lonely is the night_ by Billy Squier.” Dean pushed down his headphones once again, his eyes flicking upwards to watch Charlie, eagerly waiting for a call to come through.”

“Phone call, Dean!” Charlie called.

There it was, the stupid thing his heart did when Cas rang.

Charlie rolled her eyes at Dean’s excited puppy expression. “It’s not Cas.”

Or not.

“Put it through to line 2, I’ll answer it after a few texts.” Dean told her, just as the song was coming to a close.

“And we’re back! You’re listening to Dean Winchester on Wave radio, and you’re just in time to hear me interact with some of the listeners!” Dean’s eyes flicked to the screen in front of him, where the stream of texts coming in was displayed. “Ariel from Palo Alto says Wow, Dean, I thought I was going to be sad on Valentine’s but you sure cheered me up! Love ya.” Dean grinned. It was one of his favourite things about being a radio host; making people happy. “Glad to hear it, Ariel. Next we have a text from Aidan, he says ‘My girlfriend Krissy and I love listening to your show, especially when we’re doi-’ _wow,_ Aidan. TMI, bro. Kids listen to this station!”

 _I probably should read the texts fully before reading them on air,_ Dean thought.

"Another text from Dakota Jenner, and she says 'Dean, it's valentine's day. when are you gonna admit your crush on Cas? you're so cute together!'"

_I definitely should read the texts first._

“So, um, now I’m gonna cut to a phone call.” Dean pressed the button to answer the phone. “Hellooooo, this is Dean Winchester, how may I fulfil your listening pleasures this morning?”

“Well, like you pointed out before, children listen to this; therefore it would be a good idea not to tell you exactly how you could pleasure me, Dean.” A deep voice said, ringing through Dean’s headphones like a slap in the face.

A good slap on the face, though.

Dean almost choked on air.

Charlie was stood in the window, holding up a sign saying ‘ _payback, bitch!’._

“H-hey, Cas.” Dean took a deep breath, trying to slow his heart rate. “Was wonderin’ if you were gonna call today.”

“Wonder no more, Dean.” Cas replied. “How could I ever deny myself the pleasure of speaking to you on Valentine’s day?”

“So, no secret admirers have shown up on your doorstep and taken you out, then?” Dean asked.

“No, but I doubt I would have gone with them, anyway.” Came Cas’ answer, piquing Dean’s interest.

“Why so?”

“I have my heart set on someone specific.”

Yeah, Dean’s heart was set on something specific too; beating itself out of his  chest.

“Tha- that’s great, Cas.” Dean said, trying to quell the jealousy burning in his gut. “Who’s the lucky person?”

“I’m not sure if I should say on the radio, Dean.”

“Are you gonna confess your undying love, then?”

“I’m not sure, yet.” Cas paused. “What do you suggest I do?”

“I’m no cupid, Cas. I don’t wanna be held liable if I tell you to go for it and they turn you down.” Dean’s eyes widened. “Sh- I mean, not that they would turn you down, or not, I mean-”

“I’d appreciate your viewpoint on the matter.” Cas said smoothly, breaking Dean from his awkward rambling.

“It depends, I guess.” Dean thought for a moment. “Do you think they like you back?”

“I don’t know for sure.” Dean could nearly hear Cas’ frown through the phone. “How would I know if he did?”

“So it’s a guy?” It seemed worse, somehow, that Cas had a crush on a guy that wasn’t Dean.

“Yes.”

“Right, well. Um. I’d ask Charlie for help but she’s not really versed in knowing if guys like you, so I- um. I guess they talk to you a lot, laugh at your jokes, flirt maybe?”

Cas hums. “I suppose it is possible that he may like me, too.” He said.

“So you wanna tell him how you feel?”

“Yes, I think so. What do you suggest, Dean?”

“You need to do it in person, y’know, face to face? So he knows it’s genuine-”

“Oh- okay. I see.” Cas sounded odd.

Dean waved it off, and continued anyway. “Kiss him, maybe? It depends how comfortable you are, really. I don’t wanna sound cliché, but you just need to be yourself.”

“I- thank you for the advice, Dean.” There was a few muffled sounds coming from Cas’ end of the phone. “I’m sorry, my brother has arrived with one of his, um, _co-stars_. I have to go.”

“Oh, Okay.” Dean replied, trying not to let his disappointment leak into his tone. “Well, uh, good luck with everything. Happy Valentine’s day, Cas.”

“You too, Dean.” Cas replied, before hanging up, leaving Dean feeling dejected.

Dean cleared his throat as his eyes flicked to the clock. 10:57.

“Anyway, it’s almost time for Chuck and Becky’s show, so I’ll leave you with this song and a piece of advice- be ballsy, okay? Don’t let love pass you by, yada yada yada. You don’t wanna keep quiet then find out your crush is with someone else because you couldn’t grow some balls.” Dean ran a hand through his hair. “Regret is like, the worst feeling ever.”

Dean clicked a few buttons, and the intro to _dust in the wind_ began.

“One last thing, don’t get too drunk tonight, guys! Adios.” Dean said, and took off his headphones. The red light above the door went off.

“Are you okay, Dean?” Charlie was stood in the doorway once again, looking concerned.

Dean put on a bright smile. “’course. Why wouldn’t I be?”

Charlie didn’t look convinced. “Because-”

“Listen, Charlene, I gotta go do, uh, things. I’ll see you at the Roadhouse later, okay?” Dean stood up and began to collect his things off his desk; his phone, his keys, and his favourite Marvel mug.

“Dean-”

Dean ignored her, and with a cheery ‘ _Bye, Charlie!’_ he bounded out of the room.

 

❤

 

“Great show today, Dean.” Jess grinned, leaning in to hug Dean. Even though they only lived in Palo Alto, Sam and Jess were so buys with college that they barely ever got to see Dean. Dean didn’t mind that much, knowing his brother was safe and happy was usually enough for him, but Ellen Harvelle was another matter altogether. She’d called Sam up the week before and told him that if he didn’t come and visit him soon, she was going to go to Palo Alto herself and whack him upside the head.

Of course, Sam didn’t even think of saying no.

“Thanks.”

“We were listening to the same show, right babe?” Sam asked, sliding up to his girlfriend and wrapping an arm around her. “Because _I_ seem to recall Dean being a bitter single person who pretends not to like the Taylor Swift songs that get requested.”

“Shut up, Sammy. Not all of us wanna be stuffy lawyers, y’know.” Dean grinned. “You’re just jealous because all the girls love me because I’m on the radio.” Dean waggled his eyebrows.

Sam scanned the bar behind Dean. “And where are these girls, Dean?” He asked, an amused expression on his face.

“Well they’re not here tonight, because I knew you and Jess were coming so I, being the amazing brother that I am, decided to focus on my friends and you two!” Dean exclaimed.

“You’re so full of it.” Sam snorted.

“ _You’re_ so full of it you-” Dean trailed off, as his eyes were drawn to the open door where a new group of people were walking in; strangers, no less. It wasn’t often that the Roadhouse got any patrons that weren’t regulars. One man in particular had made Dean’s sentence cut off; his beauty seriously deserving all of Dean’s attention.

Sam and Jess’s eyes follow Dean’s gaze, and the three of them watched the group of five wander into the bar and sit down in one of the corner booths. To Dean’s surprise, Charlie spotted the group too and skipped from her position next to Jo at the bar and went to talk to the seriously hot guy that Dean was near-drooling over.

If Charlie wasn’t a lesbian, and didn’t have a Texas-sized crush on Jo, Dean would have been jealous.

Charlie held out a hand to the man, who shook it with a warm smile, and Dean almost smiled back, until he realised that would have been creepy seeing as the man wasn’t even smiling at Dean to start with.

With a shake of his head, Dean decided to distract himself with the jukebox. He needed to put on some good music before Jo got to it, and put on some cheesy love crap. He scanned the list of songs, even though he knew it like the back of his hand, by now. The buttons were basically grooved with Dean’s fingerprints.

Dean was so invested in choosing a song that he was startled when he heard a voice coming from behind him. “Hello.”

Once Dean had gotten over his initial shock, he realised the voice was familiar.

Dean turned around to see the hot stranger guy standing there, an amused smirk on his face. Dean almost swallowed his own tongue, the proximity making the guy look so much more hot than Dean had even thought was possible.

The man ran a hand through his messy dark hair, making Dean realise he’d been staring like some sort of weirdo for a touch too long.

Dean’s tongue darted out to wet his lips, before he grinned at the man. “Hey there.”

The amusement on the man’s face seemed to double as he smiled back at Dean, flashing his gums. “Someone gave me some advice, today.”

“Oh yeah?” Dean asked, wondering where he was going with it.

The man hummed, and once again, Dean felt as if he should recognise the man from somewhere. “He told me to tell my ah- _crush_ , how I feel.”

“Well, uh, don’t let me stop you.” Dean replied, feeling awkward. What were the chances that two people that Dean was interested in had a crush on someone else? Wait-

That’s when it hit him.

Dean’s eyes widened as they studied the man in front of him with more intensity. “ _Cas?”_

The man’s smile grew even larger, his azure blue eyes brightening. “Hello, Dean.”

“Wow, this is, uh- it’s weird to put a face to the name, I mean, good weird-”

“I agree.” Cas said.

“How did you-” Dean began.

“How did I know you were here?” Cas asked, and Dean nodded. “I heard you mention the bar on the radio, and when I called in, Charlie invited me to come. She said she can’t handle the UST anymore, but I’m not sure what she means by that.”

“Damn Charlie.” Dean chuckled.

“You- you don’t think it’s weird that I came here because I knew you would be here?” Cas asked, looking slightly nervous. “Because I’ll leave if you wan-”

“No!” Dean exclaimed. “I mean, I don’t think you’re being weird, Cas. You just have more balls than me, is all.”

“I’m glad, because as I was saying earlier, you gave me some advice, and I decided that I was going to act upon my crush.”

“What did he say?” Dean asked, pushing away the nausea building inside of him. If Cas was going to tell him his advice worked and he now had a boyfriend, so help him Dean was going to-

“Do you honestly not realise where I’m going with this?” Cas replied, his eyebrows drawing together slightly.

“What do you-”

Before Dean could finish his sentence, Cas placed a hand on the back of Dean’s neck and pulled him in close, and pressed a soft kiss to Dean’s lips.

“It’s you, Dean.”

Dean blinked. “What?”                                

“Do you honestly think I spent so much on my phone bill to talk to someone I didn’t have a slight crush on?” Cas asked, their faces only centimetres apart, breath mingling.

“Oh!” Dean said, cursing himself for being so stupid. Cas liked _him_.

Wait. Cas _liked_ him!

Cas apparently sensed the oncoming freak out, because he pushed Dean backwards until his back hit the jukebox and then wrapped his arms around Dean’s waist. “I have been waiting a long time to meet you, Dean Winchester.”

Cas tilted his head up once again and pressed his lips onto Dean’s, harder this time. Dean kissed back with enthusiasm, teeth grazing Cas’ lower lip. It was tender and sweet; the longing from all the months of not knowing each other pouring into the kiss.

Cas pulled his face back slightly so he was able to look Dean in the eyes. “Happy Valentine’s.” He said.

“Yeah,” Dean breathed in wonder. “It is.”

“It would be even better if we left here right now and went back to my house.” Cas said, a glint in his eye.

Dean was grabbing his hand and propelling him away before he even finished his sentence.

When they passed Sam, he looked at Dean with a smirk. “I thought you were focusing on your friends and brother tonight, Dee?”

“Oh I will be focusing, Sam. _All night.”_ Dean waggled his eyebrows, and Cas chuckled from his place at Dean’s side.

Sam scrunched up his nose _. “_ Gross, Dean.”

Jess suddenly appeared beside Sam with wide eyes. “You’re the guy, aren’t you?” She asked Cas.

Cas tipped his head to the side in confusion. “Excuse me?”

“The guy!” Jess grinned. “The one that was calling Dean on the radio!”

Cas’ cheeks coloured slightly. “Yes.”

“That’s you?” Sam gasped.

“Yeah okay, this is sweet and all but I gotta cut this party short.” Dean said, and Cas looked relieved. “Sammy, tell Jo drop my pie off later.”

With one last grin, Dean tugged Cas out of the door of the Roadhouse.

“Men and pie.” Jess sighed affectionately. “You have to admit, he’s got his priorities in order.”


End file.
